Cigar Aficionado

Sixteen square feet. That was all the space Jonathan Drew had to work with when he opened a cigar kiosk in The Mall at the World Trade Center back in 1995. Little did he know how much that kiosk would alter the course of his life, as he would forgo a career in law and build such popular cigar brands as ACID, Liga Privada, Herrera Esteli and Undercrown.

But on this day, an unseasonably warm February morning in Lower Manhattan, Drew stands beside the manmade waterfalls of the 9/11 Memorial, where the Twin Towers once stood. Wearing whitewashed jeans, a graphic T-shirt and a stark white sport coat, topped with a matching white winter hat and blue-tinted glasses, his outfit would stick out in the typical cigar shop. But on the streets of New York City, he is just another disparate soul in the throng. It's been more than a decade since he's been back in this area, and he fondly remembers the time when he was "the cigar guy" in the North Tower.

"I called my kiosk QC Cigar Company. I told everyone it stood for quality control," he says, "but really it was Queen's Counsel." This was a nod to the fact that, while he was running the kiosk, he was also studying at Brooklyn Law School to become an attorney.

Originally, he had planned to open a cigar shop near home in Brooklyn Heights, but he got a lead that the World Trade Center was looking for vendors to populate its newly rebuilt concourse level. He seized the opportunity and signed a $2,200-a-month lease for the prime retail spot, with the cigar boom in full swing. The kiosk sold brands such as H. Upmann, Macanudo, Flor de Florez, La Gloria Cubana, Fonseca and Davidoff. "Ninety-five percent of my leads as to who to call to buy cigars from came from Cigar Aficionado," he says. "The ads at the bottom would always have a telephone number to call. Back then there were no websites, but everyone had a telephone number."

Drew's phraseology is unique in the cigar industry. At times he sounds more like he's performing a braggadocio rap in a hip-hop song than answering a question or marketing a new product. Hidden underneath the verbal onslaught are the workings of a highly intelligent businessman who is not afraid to loudly share his opinions, even if he sometimes refers to himself in the third person.

"J.D. had an office at 196 Broadway. I had a dolly that I'd stack with cigar boxes and bundles," he says, pantomiming the laborious process with exaggerated movements and a smile. "Then I'd walk down Dey Street, or sometimes past the [St. Paul's Chapel] graveyard. I'd dump it out, right in the middle of the Trade Center, slice the boxes and restock the kiosk."

On Saturdays Drew would boost his income by hawking wares that weren't selling at his parents' Long Island antique shop at a street fair in Manhattan. "On Sundays, I would sleep sometimes for 24 hours. So, my work ethic—that's when it really kicked in."

His hustle paid off as his tiny kiosk did roughly $580,000 in sales in the first year. "Cigars were so hot at the time that I had lines like McDonald's." But Drew wanted his own brand. "The antiques, I knew that wasn't going to be my path forward. The law? I absolutely hated that stuff, but I did it for the cash."

In came Marvin Samel, who had attended the State University of New York at Oneonta with Drew and was working as a mortgage broker at the time. The pair had become fraternity brothers while in school, with Samel graduating a year behind Drew. Samel helped Drew to buy out an early investor in the kiosk, and the pair formed Drew Estate Inc. in 1996. He finished his legal studies that year, choosing to attend his graduation only for five minutes ("I had work to do.") The duo then enlisted La Rosa Cigars, an old-time chinchalle located on Sixth Avenue in Manhattan, to create their first brand: La Vieja Habana. Drew says he named it for the city-center of Old Havana, which in Spanish is Habana Vieja. To better appeal to customers, though, he switched the order of the Spanish words to mimic one of his favorite brands at the time: La Gloria Cubana.

At this point, Drew also became an independent sales representative for Nick Perdomo of Nick's Cigar Co. (now Perdomo Cigars). His territory included 15 states, and he hired a team to help visit cigar shops. He instructed the sales reps to also sell his La Vieja brand. While the strategy boosted La Vieja's reputation, finances were spread thin. "I had all these people working for me; that's why I was losing money," he says.

In the second year, the kiosk did more than $810,000 in sales, but much of that was done wholesale to other cigar shops. "When we added up all of our costs, we were actually losing money by selling wholesale to other shops," Samel told Cigar Aficionado in 2010.

To keep the La Vieja brand, production was moved to Perdomo's Tabacalera Perdomo factory in Nicaragua. The brand received critical praise, scoring 89 points in a May 1998 Cigar Insider tasting, and sold well. But as it was taking off, Hurricane Mitch hit Central America, and production halted.

"I had a transitional moment—it wasn't even a tipping point," he says, delving into his signature circular reasoning. "Because when you think of a tipping point, you kind of think of a line in the sand. But that line in the sand is very blurry, brotha. It's like falling in love with a woman. It's not like you fall in love with a woman and say, ‘That's it!' Falling in love with being a manufacturer of something, back when I got into it, in a world where there were no gringo guys making cigars. It was really mind warped."

Determined, he borrowed $100,000 and headed to Nicaragua to learn as much as possible about cigar production.

Jonathan Drew was born Jonathan Sann on July 5, 1969 in Babylon, Long Island, New York. Growing up in Suffolk County, he went to school in Southampton, while his parents ran their antique store. Throughout his childhood, the household was filled with aged wares.

"It was packed to the rafters," he says. "[My parents] kept all their antiques in banana boxes. Chiquita banana boxes, stacked up to the ceiling. You'd have a line from the kitchen to the living room; kitchen to the stairway. So, there was nowhere to move in my house. I hated those banana boxes."

His parents' collection of antiques may have hindered his youthful mobility, but he believes they taught him to not only appreciate history, but to understand "the moment in time when something was created and why it was created and what was the lineage behind the product."

A self-described "thrasher kid," Drew was a fan of heavy metal music at a time when it began to converge with hip-hop. While the lyrics, the bravado, the feuds and the rawness of hip-hop spoke to him, Drew also had great admiration for the producers behind the artists and how they distributed and cross-promoted musicians.

After high school, Drew headed to SUNY Oneonta as a political science major with a minor in business. In the final semester of his senior year, he landed an internship working under then New York Sen. Alfonse D'Amato in Washington, D.C. "[His staff] used to call me ‘Baby Alfonse' because they said I looked a lot like him," recalls Drew.

One night, as he was waiting for the Senator outside a function, D'Amato's driver reached into the politician's stash of cigars. He handed Drew his first cigar, a Partagás Serie D No. 4, and the two lit up. It was love at first puff.

"The first cigar was beautiful," says Drew. "That's the thing: If you start off with a good stick that isn't overpowering, doesn't knock you on your ass—you know, turn you off—the chances of you becoming a cigar enjoyer is higher."

Drew envisioned himself entering politics and enrolled in law school. He worked on D'Amato's 1992 reelection campaign, and as a legal assistant from 10:30 at night to 7:30 in the morning, three or four nights a week. "It was going to be a career job. I got $15 an hour and $18 a night for dinner," he says. "I opened the kiosk to be able to pay for law school, which is expensive. Plus, I needed cash in hand, because I always liked the ladies and I liked to go out and I liked to have fly gear." He winks.

And, of course, he continued to smoke cigars, everything from H. Upmann Lonsdales to Cuban Davidoffs. But he wasn't just a casual smoker, but a lover of the leaf who had a deep interest in learning about the stories behind the cigars.

"Brands excite me. Brands get into me. I would walk into the stores and pepper the owner or the manager or whoever was in the store, with so many questions about the history of the brand," Drew says. "I was really bombarding them with questions that were not so much about how does the cigar taste. I was more interested in the who and the why. I valued [a brand owner's] lineage. I valued their journey. I valued their results."

At this time another medium also caught his eye: graffiti. Drew would puff a cigar and walk through Manhattan's SoHo neighborhood, craning his neck to see the intricate tags, murals and stencils of various street artists. Some of the art resonated deep with Drew. "There's a rawness to graffiti that I need," he says.

Today, Estelí, Nicaragua is a thriving municipality, teeming with dozens of cigar factories surrounded by tobacco fields. In 1998, when Drew arrived, it was a vastly different landscape, with only a few cigar companies that called it home, almost all owned by expatriate Cubans. "I was the only gringo out in Estelí," Drew says, proudly. "Go out to Estelí today, and you bump into this guy or this gringo guy. Back then, there was nobody."

Drew proved himself through hard work and dedication, at times even sleeping on a mattress on the floor of a room in the Tabacalera Perdomo factory as he worked to develop a cigar brand that combined his affinity for hip-hop and street art: ACID. He had conceived the brand with Samel and friend Scott "Acid" Chester, a New York-based designer.

ACID cigars are infused with essential oils, herbs and botanicals, but unlike a typical flavored cigar, they are handmade and use long filler tobaccos. The various lines are adorned with brightly colored bands reminiscent of graffiti. When ACID debuted at the 1999 cigar trade show, it was an immediate success. Many millions of ACID cigars have been sold since, and it is fair to credit the brand with making the infused cigar market as large as it is today.

"At first I didn't think it would sell," says Jeff Borysiewicz, who owns four cigar retail stores in Florida, including the enormous Corona Cigar Co. in Orlando. "I just didn't know about the name. But it sells phenomenal and is popular with all kinds of smokers, young guys to middle-aged men."

In 2005, Drew and his company decided it was time to dive into the traditional cigar market. "We were known as the ACID guys, or the infused guys. We wanted to be the Drew Estate cigar company. People wondered why we didn't just make ACID. Less inventory, less problems," he says. "But it wasn't fun just to make that. I have a lot of things I got to make. If you're an artist, you're not doing only one show. You want to get to the next thing."

The following year the company debuted Château Real, an eight-size line that averaged 87 points in a May Cigar Insider vertical tasting. However, it was not the mega-hit Drew had hoped for, and he refers to it as "a total failure."

Drew believes Château is a good cigar (the company still makes it), but that it was too safe a bet when it debuted. It didn't possess any swagger or style, two attributes that Drew sees that help define part of the core values of Drew Estate. He learned from the experience.

"You could make the best tasting cigar on the planet, but if your aesthetics aren't right—packaging, graphics, the boxes and the place that it takes you to, if that ain't right, no matter how good the cigar, it's just probably not going to be a super successful brand. The trifecta is when you make a cigar that tastes really great, package it and position it well, and you make the cigar a winner, meaning great construction."

Drew and his team hit a trifecta with the brand they released in 2007: Liga Privada No. 9. While many companies were touting puros, Liga was a four-country blend that included Brazilian Mata Fina (rarely used at the time) wrapped in expensive, tantalizingly dark, broadleaf tobacco grown in Connecticut. It debuted in one size, a 6-inch-by-52-ring-gauge parejo. The bands appeared to be handwritten and resembled labels found in distillation plants or tasting laboratories. The brand quickly became a cult hit. 

"Guys that smoke ACID don't just smoke only that brand," says Borysiewicz. "They trust Drew Estate, and many will plunk down the money to give Liga a shot."

Even more importantly, Liga's success demonstrated to the cigar industry that Drew Estate could compete in the traditional market. Drew sees Liga Privada No. 9, which he estimates sells about 500,000 each year, as the company's "OpusX." Fans eagerly await new shipments of Liga Privada and its offshoots, T52 and the Único Serie. In 2013 and 2014, Liga Privada topped Cigar Insider's retailer survey when it was named Hottest Brand in the United States. Additionally, the cigar continues to score well within the pages of Cigar Aficionado, earning a spot in the magazine's Top 25 Cigars of the Year list in 2014 and 2015.

The same year that Liga Privada hit the market, Drew Estate consolidated its cigar production when it moved into a new production facility named La Gran Fabrica Drew Estate, which today is the largest handmade cigar factory in Nicaragua, if not the world. In the years to follow, Drew Estate would build on Liga Privada's success with a slew of brands that stand out in their own ways.

While most cigar blends are conceived by a designated blender, a team of blenders or a brand owner, Undercrown started off as a cigar that the factory's rollers created for themselves. It has many of the same tobaccos found in Liga, but replaces the wrapper with Mexican San Andrés.

In 2011, the company launched My Uzi Weighs a Ton (MUWAT), named after a lyric from a Public Enemy song. The line debuted in three lengths all at 60-ring gauge and packed in plain brown paper. "People freaked out about the idea," says Drew. "It was a cool brand and it's still out there. It's not our biggest brand, but it was never meant to be."

That same year, Drew Estate brought in Willy Herrera, the former cigar blender from Miami's El Titan de Bronze factory, to create a signature, "Cubanesque" blend. Herrera, who is of Cuban descent, made the Herrera Esteli brand, which included a figurado called Piramide Fino that was named Cigar Aficionado's No. 8 Cigar of 2013, a first for Drew Estate.

Next Drew extended MUWAT with Kentucky Fire Cured in 2013. The blend contains Kentucky and Virginia tobaccos—normally used for dry and moist snuff—that have been fire cured over hickory, maple and oak woods. This method infuses it with a smoky quality, similar to a peated Scotch.

By 2014, Drew Estate was producing roughly 25 million handmade cigars per year and had amassed an inventory of more than $20 million worth of tobacco. Across from La Gran Fabrica Drew Estate, the company opened a new 61,000-square-foot warehouse solely as a tobacco storage and sorting facility for leaf from Nicaragua, the Dominican Republic, Ecuador, Honduras, Brazil, Mexico, Cameroon and Indonesia. Herrera, now officially its master blender, released Norteño. (The Robusto Grande would later become the No. 7 Cigar of 2016, scoring 94 points.)

Additionally, the company mastered the art of the in-store event, employing teams of sales reps who didn't just sell cigars but established a connection with customers and created a loyal fan base.

"We've learned to value our consumers in a very unique way, and it's noticeable," says Drew. "If you take for granted the people who enjoy your products, you don't get to learn from them and you don't get to share the experience with them. For God's sake! We're all numbers now. You walk into a bank, they don't care what your name is. You call a big company and you're only a number now. So, when you can turn around and J.D. can remember a person and take a moment and actually dedicate some of your time back to him. That's a really big thing."

And then Drew Estate dropped another bomb on the cigar industry, only it wasn't a new brand.

About 30 months ago, Drew Estate announced that it had been acquired for an undisclosed sum by mass-market behemoth Swisher International Inc., best known for making Swisher Sweets and other machine-made cigars.

The move caught loyal fans of Drew Estate and its retail partners by surprise. For Drew, who owned a majority stake in Drew Estate along with Samel, the time had come to sell.

"It was the time because the company had grown so big that I couldn't finance the damn thing anymore. We grew so fast over the last 20 years that we didn't have certain stability factors behind us to withstand a trial such as a natural disaster or fire. And that really scared me because I don't like risks, unless it's creative risk," says Drew.

According to Drew, a few companies had approached him with offers to buy out Drew Estate, including another premium cigar company and a large cigarette company. But Drew felt that the Swisher deal not only had good timing financially, but that the organization, which is privately owned by the Ziegler family, shares a lot of the same attributes, chiefly provocative brands. "I think that [Swisher] really fought for us because Drew Estate felt good to them," he says. "They love the company and don't want to ‘Swisher-ize' it."

After the sale, Drew stepped back in his leadership role, becoming more of a brand ambassador, traveling the country and engaging consumers at cigar events. It was during this time that he also "took a deep dive," as he puts it, into the spirits industry, studying the intricacies of the marketplace and working on making connections. Spirits, particularly Bourbon, had always been dear to Drew, and he had envisioned himself entering that industry. He purchased 10 acres in Orlando, Florida, with the hopes of building a distillery on it. Last April, he debuted three spirits brands under the company John Drew Brands. One expression in particular stands out. Dubbed Brixton Mash Destroyer in honor of London's bohemian neighborhood, the liquid is a blend of Kentucky Bourbon and rum made from Florida-grown sugarcane.

In his absence, a shakeup was happening for Drew Estate. In July 2016, on a day that most of the premium cigar industry was traveling to the annual trade show, the company announced that Glenn Wolfson had been hired as the company's new chief executive officer, replacing Michael Cellucci, who had been at the company for 16 years.

While Drew doesn't offer any specifics as to what happened, his overall thoughts are that Drew Estate post sale to Swisher had become complacent. "Our aspirations became a little bit focused off of the core characteristics of what distinguished our brands from others. When you have brands like Drew Estate that are so engaging that people believe that they are their brands," says Drew, passionately. "When we sold Drew Estate [our customers] took it personally. The Drew culture was no longer driven with the hard iron fist of Jonathan Drew. It just was not unified. We were in the state of utter chaos, and we weren't even Drew Estate for the last two-and-a-half years. It was some concoction."

Herrera believes Drew Estate strayed from its roots "and what makes us different. Stemming from camaraderie within all the way to the execution of events. The ball was getting dropped a lot and there wasn't enough communication between teams. Also, egos started getting in the way."

In January, the company announced that as part of a multiyear deal, Drew had been named president, charged with overseeing the company's entire portfolio of brands.

Herrera is excited to see Drew return to the company and has great respect for Wolfson. "The biggest thing about Glenn is he's transparent. There is no more guessing and wondering. Now I know where I stand and what I need to do," he says. "With Jonathan, his strengths are his marketing ideas and new concepts, along with the execution of those ideas."

Drew is quick to say that there were some good things to happen in his absence, such as streamlining back-end software for improved efficiencies. "But now we are returning to our core, which is brands, brands, brands!" he says, slamming the bottom of his fist into his open palm.

After much probing, Drew does offer this nugget: "We are considering buying land and farming imminently in our core component areas, which are Nicaragua, Brazil, Connecticut and Mexico." Growing its own tobacco would be a new—and potentially significant—venture for Drew Estate, which is one of the largest buyers of premium tobacco in the cigar industry.

One plan is for certain: In honor of Liga Privada's 10-year anniversary, Drew Estate plans to release its "best Liga yet," says Drew, a Liga Privada Sungrown Aniversario covered in Ecuador Sumatra wrapper. Instead of Liga blue, the color scheme will be mainly black. The idea was to create "something a little milder than Liga Privada," says Herrera, "because not all smokers can handle the original Liga No. 9 and T52."

Two sides of Jonathan Drew are immediately evident: the marketing genius and the quirky personality whose unusual antics come off as brash to some. But if you hang around Drew for long enough, a third side emerges. Underneath all his swagger is a compassionate man who knows how to listen and genuinely cares not only about his customers, but about people. It's as if he plays a character when talking about cigars, simultaneously an enigma and an open book.

He sits in the offices of Cigar Aficionado, his legs bouncing rapidly up and down. He's searching through his iPhone for a note he calls "The Forgotten," a list of his brands that he feels have failed for one reason or another. It includes brands like Kahlua, Nosotros, Cigar Repair, Mayorga, Château Real and numerous others.

"If you can't connect to your pain, if you can't connect to your loss, if you can't connect to your failure, then you can't stay raw and you can't keep it real," says Drew. "It's a reminder that you ain't shit. It's about the team with me. Bringing the brands to life is illustrating the details. I'm going to help the creative forces at Drew Estate have fun again. No one makes cigars better than Drew Estate. I really mean that."